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Open Access Publications from the University of California

Synthesis of o-quinodimethanes and benzocyclobutenes from dimethyl squarate

  • Author(s): Ezcurra, JE
  • Moore, HW
  • et al.

Selected 3-alkylidene(and benzylidene)-4-allenylcyclobutenes were shown to undergo an unusual thermal ring expansion to o-quinodimethanes and thus to benzocyclobutenes upon electrocyclic ring closure. The mechanism of this rearrangement is envisaged to involve ring opening of the starting cyclobutenes to the corresponding octa-1,2,4,6,7-pentaenes which lead to the quinodimethanes upon ring closure. © 1993.

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